Fluorescent probe for targeting detection and cancer cell inhibition and its preparation method and use

A technology of fluorescent probes and cancer cells, which is applied in the field of fluorescent sensors, can solve the problems of lack of targeting, and achieve the effect of simple preparation method and convenient operation

Inactive Publication Date: 2015-01-07
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the current problem that most of the BODIPYs dyes are distributed in the cytoplasm when used in live cell imaging and do not have targeting, one of the purposes of the present invention is to provide a fluorescent probe for targeted detection and inhibition of cancer cells, so The fluorescent probe has the functions of targeting and inhibiting cancer cells at the same time; the second purpose is to provide a method for preparing a fluorescent probe for targeted detection and inhibition of cancer cells, the preparation method is simple and easy to operate; The third is to provide a fluorescent probe for targeted detection and inhibition of cancer cells

Method used

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  • Fluorescent probe for targeting detection and cancer cell inhibition and its preparation method and use
  • Fluorescent probe for targeting detection and cancer cell inhibition and its preparation method and use
  • Fluorescent probe for targeting detection and cancer cell inhibition and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] (1) Weigh palladium chloride (PdCl 2 , 0.1383g), copper bromide (CuBr 2 , 10.4105g) was added to a 250mL round bottom flask, acetonitrile (1.26mL) and toluene (63mL) were added, 4-ethynylbenzaldehyde (2.0g) was slowly added, and the coupling reaction was carried out while stirring at 25°C. Stop the reaction after reacting for 11h, filter the mixture in the flask with a Buchner funnel, and spin the filtrate to obtain the crude reaction product 1. After dissolving the crude product 1 with 5mL chloroform, dissolve the crude product 1 with petroleum ether:dichloromethane=1:1 As eluent, separated by column chromatography and vacuum dried to obtain 4,4'-((1E,3E)-1,4-dibromo-1,3-butadiene-1,4-diyl)diphenyl formaldehyde;

[0064] (2) Weigh 573mg 4-formylphenylboronic acid pinacol ester and add it to a 250mL three-neck flask, add 100mL CaH 2 Dried dichloromethane, sealed with a rubber stopper and passed through N 2 After 30 minutes, add 565 mg of 1,4-dimethylpyrrole, add 0.1...

Embodiment 2

[0074] (1) Weigh palladium chloride (PdCl 2 , 0.1383g), copper bromide (CuBr 2 , 10.4105g) was added to a 250mL round bottom flask, acetonitrile (1.26mL) and toluene (63mL) were added, methyl 4-ethynylbenzoate (2.0g) was added slowly, and the coupling reaction was carried out while stirring at 25°C. Stop the reaction after reacting for 11h, filter the mixture in the flask with a Buchner funnel, and spin the filtrate to obtain the crude reaction product 1. After dissolving the crude product 1 with 5mL chloroform, dissolve the crude product 1 with petroleum ether:dichloromethane=1:1 As eluent, separated by column chromatography and vacuum dried to obtain 4,4'-((1E,3E)-1,4-dibromo-1,3-butadiene-1,4-diyl)diphenyl Methyl formate.

[0075] (2) Weigh 573mg 4-formylphenylboronic acid pinacol ester and add it to a 250mL three-neck flask, add 100mL CaH 2 Dried dichloromethane, sealed with a rubber stopper and passed through N 2 After 30 minutes, add 565 mg of 1,4-dimethylpyrrole, ad...

Embodiment 3

[0085] (1) Weigh 8 mg of DIBODIPY-DICHO prepared in Example 1 and dissolve it in 15 mL of dried N,N-dimethylformamide (DMF), add 8 mg of polypeptide (cc-259 for short, its structure is given by Composed of 11 amino acids, including glycine (Gly), histidine (His), isoleucine (Ile), serine (Ser), valine (Val)), the oil bath was stirred at 30°C for 40 hours, and the air pump was used to directly Blow dry the solvent DMF. The dried product was then dispersed in 5 mL of dimethyl sulfoxide (DMSO) to remove unreacted raw material DIBODIPY-DICHO. Then add 200mL of distilled water thereinto, after stirring evenly, put the mixed solution into a dialysis bag with a molecular weight cut-off of 1000, immerse the dialysis bag in distilled water and let it stand for dialysis for 48 hours, take out the solution in the dialysis bag after dialysis, freeze it with liquid nitrogen, Freeze and vacuum dry in a freeze dryer to obtain solid powder DIBOODIPY-PEPTIDE.

[0086] Among them, the polypep...

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Abstract

The invention discloses a fluorescent probe for targeting detection and cancer cell inhibition and its preparation method and use, and belongs to the field of fluorescent biosensors. The fluorescent probe is a 1,4-tetraarylbutadiene derivative containing 4, 4', 4''-di-4-difluoro-4-borata-3a-azonia-4a-aza-s-indacene (BODIPY). The preparation method comprises that 4,4'-((1E, 3E)-1,4-dibromo-1,3-butadienyl-1,4-dily)dibenzaldehyde (or methyl 4,4'-((1E, 3E)-1,4-dibromo-1,3-butadienyl-1,4-diyl)dibenzoate) and BODIPY pinacol ester undergo a Suzuki reaction in the presence of a tetrakis(triphenylphosphine)palladium as a catalyst to produce the fluorescent probe or BODIPY-DICHO and a biomolecule undergo a one-step Schiff base reaction to produce the fluorescent probe. The preparation method has simple processes and is convenient for operation. The fluorescent probe has functions of targeting marking and cancer cell inhibition and can be used as a latent anticancer drug.

Description

technical field [0001] The invention relates to a fluorescent probe for targeted detection and inhibition of cancer cells, a preparation method and its use, in particular to a 1,4-tetraaryl group containing a 4,4',4"-difluoroboron dipyrrole group A butadiene derivative fluorescent probe and a preparation method thereof, the fluorescent probe can be used in bioluminescent imaging technology for targeted detection of cancer cells, belonging to the field of fluorescent sensors. Background technique [0002] Fluorescence imaging technology is an indispensable technology for biomedical research, clinical diagnosis, and drug detection. An ideal fluorescent probe should have suitable excitation and emission wavelengths, higher brightness, better biological stability, lower biological toxicity, and better photostability. Especially for live cell and in vivo imaging, the balance of water solubility and lipid solubility is the key condition to achieve higher membrane permeability. H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64A61P35/00
CPCC07F5/02C09K11/06C09K2211/1022G01N21/6428
Inventor 董宇平陈笛笛冯霄佟斌石建兵顾尚志
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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